Water → 2-Iodo-4-methyl-6-nitroaniline

HRID 326646

Reaction equation

HRID 326646 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[I:12]Cl.O>C(O)(=O)C>[NH2:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][C:5]([CH3:8])=[CH:6][C:7]=1[I:12]

Participants

5

Reactant 3

HCID 962WaterHCID 69784-Methyl-2-nitroanilineHCID 24640Iodine chloride

Product 1

HCID 197351992-Iodo-4-methyl-6-nitroanilineYield 25.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-amino-3-nitrotoluene (30.4 g) in acetic acid (250 ml) was refluxed with iodine monochloride (65.0 g) for 7 h with stirring, then was cooled and added to excess water. The precipitate was filtered off, washed with aqueous sodium sulfite and after column chromatography yielded 4-amino-3-iodo-5-nitrotoluene (14.2 g). δ (360 MHz, DMSO-d6) 2.19 (3H, s, CH3), 6.88 (2H, bs, NH2), 7.88 (1H, d, 2-H) and 7.94 (1H, d, 6-H).

Workup

  1. temperaturewas cooled
  2. filtrationThe precipitate was filtered off
  3. washwashed with aqueous sodium sulfite

Sources & evidence

ORD record
ord-8fa813648eaa4bf4aac429db349dbe1b
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Linked notes

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